


Date My Mom: Supernatural Edition

by Petrichora_Vellichor



Category: Supernatural
Genre: Alternate Universe, Date My Mom, Date My Mom/Supernatural crossover, Gabriel is simultaneously the worst brother in the world and the best, Implied/Referenced Homophobia, M/M, Pre-Slash, basically Cas goes on dates with Linda Rowena and Mary to see which of their son's he'd like to date, so yeah this is basically that old MTV show but with Supernatural characters
Language: English
Status: Completed
Published: 2019-03-19
Updated: 2019-03-19
Packaged: 2019-11-24 11:11:27
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,465
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18164444
Author URL: https://archiveofourown.org/users/Petrichora_Vellichor/pseuds/Petrichora_Vellichor
Summary: Inspired by a Tumblr prompt: Thanks to a petty act of revenge on his older brother Gabriel's part, Cas finds himself a reluctant participant on MTV's "Date My Mom." After barely managing to survive his first two dates, he is pleasantly surprised by the third mother he meets. Maybe going out with Mary Winchester's son Dean wouldn't be such a terrible thing after all?





	Date My Mom: Supernatural Edition

**Author's Note:**

> Endless thanks and credit to [mattzerella-sticks](https://mattzerella-sticks.tumblr.com/) for coming up with such a fabulous prompt and graciously allowing me to turn it into a ficlet. I hope this is somewhat close to what you had in mind.

As he sat glumly outside the café waiting for his third and final date, Cas wondered how he’d fare in court if he were to actually murder his older brother. 

_Yes, Your Honor, I did kill Gabriel, but in my defense, he was an idiot who did idiotic things, like signing me up for a dating show just because one of us didn’t think the coffee table was an appropriate place to display pornographic magazines, even if they were apparently, and I quote, “collector's items, you great big bag of dicks!”_

Cas sighed and scrubbed a hand down his face. No, that probably wouldn’t be enough to sway a jury. Then again, he was fairly certain that incarcerated felons were significantly less likely to be ambushed by MTV vans and gleefully vindictive siblings on what was supposed to have been a nice, quiet Saturday spent studying for an upcoming anatomy exam. So, perhaps prison life did have its perks after all...

Shaking his head to clear the thought, Cas checked his watch. _Any minute now..._

Just one more date, just one. Then he’d pick the son whose mother had scared him the least, the show would arrange for their date the next evening—Cas was desperately trying not to think about _that_ part of this whole arrangement—and he could finally go home and put this whole god-forsaken day behind him.

And oh, what an absolutely _exhausting_ god-forsaken day it had been...

Cas’s first date, a Ms. Linda Tran, had scarcely let Cas get his name out before she’d begun grilling him on everything from his grade school GPA to what he planned on doing with the rest of his life and just why, exactly, he thought he was good enough for her son, Kevin. Caught supremely off-guard and feeling more like he was at a job interview rather than on a date, Cas had fumbled through his responses, barely managing to get in any questions of his own. Suffice to say, he had been more than a little relieved when their time together was finally up. 

The next mother, Rowena MacLeod, had seemed more interested in securing Cas for herself. She’d brushed off most of his polite questions about her son with a dismissive wave of her hand. “Oh, Fergus is a mean, sullenly little thing,” she assured him in a lilting Scottish accent. “I’d much rather talk about _you_ , tweetie pie...” 

She’d spent the next hour asking Cas some rather personal questions that might have passed as innocent had it not been for the heated gaze that accompanied them. When Cas had hesitantly mentioned that he was majoring in biology with the eventual hope of becoming a pediatrician, Ms. MacLeod let out a delighted chortle and reached across the table to lay a delicate hand on his forearm, crooning about how the world needed more “handsome angels” like Cas and smiling in a way that Cas, despite his admitted lack of experience in flirting, was certain qualified as “sultry.” 

No sooner had Ms. MacLeod left than Cas flagged down the nearest waiter to request a shot of whatever liquor they had on hand (none, because his luck was just that wonderful lately). He’d had to settle for a glass of red wine, which he’d practically chugged, remembering only after the fact that he had various cameras trained on him from a distance and just barely managing to suppress a stream of frustrated expletives. No sense in giving the film crew even more to edit out.

Now, as he leaned over the table with his head in his hands and reflected on the disaster that had been his day so far, Cas found himself wondering if Gabriel had had a hand in picking the women Cas had met with. Based on his limited understanding of how the show worked, he didn’t think so, but the way his day had been going so far, it wouldn’t at all surprise him.

“Hi, sorry I’m late. Are you the one I’m meeting?”

Cas started at the words, lifting his head to find a woman with short, wavy blonde hair standing at the opposite side of his table. She indicated the vacant chair and clarified, “For the TV show, I mean. You’re supposed to decide if you want to date my son or something?”

“Oh! Yes, sorry, that would be me.” Cas stood to greet her. “My name is Castiel Novak, or Cas. It’s nice to meet you, Ms...?”

“Winchester, but Mary’s fine. Good to meet you, too, Cas.” She shook Cas’s hand, and they both sat as a waiter approached and took Mary’s order (“Large coffee, black, no sugar, thanks.”). Once the waiter left, Mary gestured at the empty wine glass still on the table, an amused glint in her eyes. “So, rough day?”

Cas sighed. “Very. My brother Gabriel signed me up for this show without my knowledge or permission, so today has been...interesting, to say the least.”

Mary arched an eyebrow. “Just to be clear, though, you _are_ single and you _are_ interested in men, right? Because other than Dean, all I have is Sam, and he’s got a girlfriend, so...”

Cas flushed, hoping he hadn’t come across as rude. “Yes, I am single, and yes, I am interested in men. My apologies: I didn’t mean to suggest I wasn’t taking this seriously or that I don’t appreciate your time, just that this whole experience has been a bit of a surprise.”

“Well, you’re a trooper for going along with it,” said Mary, smiling. “Most people would have refused.”

“I thought about it,” admitted Cas, “but since it’s my brother’s fault that the production crew came all the way out here, I felt it was my responsibility to participate.”

“Sounds like your brother’s quite the prankster.”

“He is. But he also took me in when I was in high school and I...needed somewhere to go,” Cas said, tripping over the words as they came out. He glanced up in nervous apology and, finding nothing but soft understanding in Mary’s expression, cleared his throat and continued more smoothly. “I’ve lived with him ever since. We’re very different, and there are times, like today, when he makes me want to pull out every strand of my hair, but he’s my family, and he’s always been there when it mattered.”

“Good.” Mary’s coffee arrived, and she thanked the waiter before leaning forward and giving Cas a conspiratorial smile. “So, how should we do this? Do you want to tell me a little more about yourself, or would you rather I tell you some embarrassing stories about my son and give you an idea of what you’d be getting yourself into?”

Cas couldn’t help it; he smiled back. “The latter, if you don’t mind.”

“Hey, I’m a mom: I never need an excuse to talk about my kids. Hmm, let’s see...Well, there was the time he was three and playing in the front yard. I turned my back for one minute to chat with the neighbor, and the next thing I know, Dean’s hollering about how there’s a giant snake trying to eat him.” Mary smirked. “New garden hose. He fell and got tangled.”

"You’re kidding.”

“Nope, dead serious. Boy still hates snakes to this day. Snakes, and flying.”

“Flying?”

“Mm-hm, found _that_ out about two years later. It was Sam’s first Christmas, and we wanted to spend the holidays with some friends of ours in South Dakota. Weather was pretty bad that year, so I told John we should fly instead of driving. Yeah, big mistake. Our plane hit some turbulence about half an hour into the flight. Nothing major, but enough to rattle everyone around a bit, and Dean was _convinced_ we were going to crash. He spent the rest of the flight clinging to my arm and screaming at the top of his lungs, and that set Sam off, which upset Dean even more, so then they were _both_ inconsolable, and John and I got to be _those_ parents with the screaming kids.” Mary took a sip of her coffee. “So, if the producers plan on sending you and whoever you pick skydiving on your first date, Dean might not be the best choice.”

Cas grinned. “I believe we’ll be keeping both feet on the ground, but I’ll bear that in mind, just in case.”

“Good boy.” Mary winked. “But I should probably quit it with the phobias. Wouldn’t want you thinking Dean’s afraid of his own shadow.” She laughed. “Actually, he tried to _fight_ his own shadow once.”

“When did that happen?”

“Morning after we brought Sam home from the hospital. So, post-snake, pre-plane. Dean was four and _very_ excited to finally meet his little brother. He snuck out of his room that night to sleep next to Sam’s crib, and I guess when the sun came up, he saw his shadow on the floor and thought it was going after Sam, so he did what any good big brother would do: dove on top of it and tried to pound it into the carpet while screaming for John and me to come save Sammy from the monster.”

Cas smiled at the mental image, a warm feeling spreading through his chest. “He and Sam are close, I take it?”

“Mm, especially when they were little. Sam followed Dean around like Dean’d hung the moon, which meant that if Dean got up to mischief, then Sam was usually right there with him.” Mary sighed and pinched the bridge of her nose. “I remember this one time when Dean was seven and Sam was three. I was at work, and it was John’s day off, so he was at home with the boys. He’d been putting up Halloween decorations while the boys played outside in their costumes, and he went inside real quick to use the restroom and left his ladder propped up against the house. Dean thought it would be a good idea for him and Sam to climb up on the roof and jump. They were Batman and Superman that year,” added Mary, shrugging helplessly at Cas’s widening eyes, “so the story _I_ got was that they thought they could fly. They couldn’t. Sam ended up with a broken arm, and Dean cut his foot on a rock and needed a few stitches, but thankfully, that was the worst of it. Needless to say, we had a _long_ talk that night about how the roof was off limits.”

Cas shook his head. “I can imagine. Gabriel and I had a similar lesson when we were young. There was a large oak tree on our property, and Gabriel used to climb up onto one of the higher branches and hang upside-down whenever he wanted to irritate our nanny. Somehow, he convinced me to join him one day when I was five or six. One minute we were clambering up while Naomi yelled at us to get down, and the next—” Cas raised his hands and made a snapping motion “—the branch we were on broke, and down we went. Gabriel managed to grab me so that I landed on top of him when we hit the ground.” Cas looked down at his coffee, using his thumb to nudge at the cardboard sleeve. “Neither of us was seriously hurt, but our father had the tree chopped down the following day.”

Mary regarded him carefully, brow furrowed and looking as though there were questions she wanted to ask, but after a moment, her expression softened into a kind smile. “Enough about the past: let’s talk about now. Can’t exactly convince you to pick my son if the only way you can imagine him is with baby teeth.”

Cas chuckled, abandoning his coffee and folding his arms on the tabletop. “Good point. So. Present-day Dean. What can you tell me?”

“Based on all the tiny print I had to read, a detailed physical description’s a no-go, but he’s about your age and height, I’d guess, and he’s in his third year at Kansas State."

Cas tilted his head, intrigued. “I go there too. What’s Dean’s major?”

“Mechanical engineering. From the time he was old enough to walk, that boy’s loved taking things apart and figuring out how they work. He pretty much rebuilt his father’s old ‘67 Chevy Impala after the accident.”

“Oh, I’m so sorry, I--”

“No no, _I’m_ sorry, that probably sounded way worse than it was. The car was stolen a few years back and ended up totaled, and before it could get hauled off to the junkyard, Dean asked John if he could have it instead. John said that if Dean was able to fix the car, he could keep it, and Dean did.” Mary beamed. “John’s a mechanic and taught Dean cars from a young age. He was so proud.”

Cas smiled. “I can see why. That’s no small feat, rebuilding an entire car. I’ve, uh, never been very handy myself.”

“Oh, me neither. That’s why I’m a social worker and not a mechanic. People, I can help; cars, though, those are best left to John and Dean. So,” she said, taking a sip of her coffee, “you mentioned that you go to Kansas State. Have you picked a major?”

“Yes, biology, third year. I’d like to be a pediatrician someday.”

“Ah, so there’s a chance my son could soon be dating a future doctor. Nice.”

Cas laughed, and he spent his remaining time with Mary learning as much as he could about Dean, from his taste in music (“Pretty sure Led Zeppelin’s still at the top of that list, but classic rock in general’s usually a winner.”) to his favorite food (“Pie, always and forever.”) to what he watched on TV (“He’ll be furious that I told you this, but have you ever heard of _Doctor Sexy_?”). 

When the crew signaled that their time was up, Mary told Cas it had been nice meeting him and that she hoped he had fun with whoever he ended up choosing. “Although I’ll obviously be keeping my fingers crossed on that front,” she added with a smile, before waving and heading off to the car that was waiting to take her to the nearby park where Cas would face the mothers once again and choose one of their sons to go on a date with. As the producer sat down across from Cas to go over the procedure and how Cas would have to draw things out for dramatic suspense by first revealing the sons he _didn’t_ want to date and saving his final choice for last, Cas found that he was only half listening. 

He was too busy wondering if wherever he and Dean went on their first date would serve pie.

**Author's Note:**

> A/N: So, should I write a second part to this with the first date, yea or nay?
> 
> (Also, come say hi over on [Tumblr](https://petrichoravellichor.tumblr.com/)!)


End file.
